CN111187169B - 氟苯衍生物和苯甲酸次氟盐衍生物的制备工艺 - Google Patents
氟苯衍生物和苯甲酸次氟盐衍生物的制备工艺 Download PDFInfo
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- CN111187169B CN111187169B CN202010066834.8A CN202010066834A CN111187169B CN 111187169 B CN111187169 B CN 111187169B CN 202010066834 A CN202010066834 A CN 202010066834A CN 111187169 B CN111187169 B CN 111187169B
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- benzoic acid
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- 238000006460 hydrolysis reaction Methods 0.000 description 1
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- 239000006223 plastic coating Substances 0.000 description 1
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- 230000036632 reaction speed Effects 0.000 description 1
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- 230000000717 retained effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
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- 238000001694 spray drying Methods 0.000 description 1
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- 239000010936 titanium Substances 0.000 description 1
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Images
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- C07C71/00—Esters of oxyacids of halogens
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
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- B01J19/08—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor
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- B01J19/122—Incoherent waves
- B01J19/123—Ultraviolet light
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- B01J19/245—Stationary reactors without moving elements inside placed in series
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- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/30—Loose or shaped packing elements, e.g. Raschig rings or Berl saddles, for pouring into the apparatus for mass or heat transfer
- B01J19/305—Supporting elements therefor, e.g. grids, perforated plates
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
- B01J8/02—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with stationary particles, e.g. in fixed beds
- B01J8/0278—Feeding reactive fluids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/361—Preparation of halogenated hydrocarbons by reactions involving a decrease in the number of carbon atoms
- C07C17/363—Preparation of halogenated hydrocarbons by reactions involving a decrease in the number of carbon atoms by elimination of carboxyl groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
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- B01J2219/00051—Controlling the temperature
- B01J2219/00121—Controlling the temperature by direct heating or cooling
- B01J2219/00128—Controlling the temperature by direct heating or cooling by evaporation of reactants
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J2219/08—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor
- B01J2219/0873—Materials to be treated
- B01J2219/0875—Gas
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- B01J2219/08—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor
- B01J2219/12—Processes employing electromagnetic waves
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- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/32—Details relating to packing elements in the form of grids or built-up elements for forming a unit of module inside the apparatus for mass or heat transfer
- B01J2219/332—Details relating to the flow of the phases
- B01J2219/3325—Counter-current flow
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
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- Electromagnetism (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
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- Thermal Sciences (AREA)
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Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5420364A (en) * | 1992-07-09 | 1995-05-30 | Bayer Aktiengesellschaft | Process for the preparation of halogenated aromatic compounds |
WO2003064371A1 (fr) * | 2002-02-01 | 2003-08-07 | F2 Chemicals Limited | Synthese d'agents de fluoration |
WO2015050379A1 (fr) * | 2013-10-01 | 2015-04-09 | 광주과학기술원 | Nouveau dérivé de quinolinone et son utilisation |
CN108250176A (zh) * | 2016-12-19 | 2018-07-06 | 上海惠和化德生物科技有限公司 | 一种氟代碳酸乙烯酯的快速连续流合成工艺 |
CN110115966A (zh) * | 2019-06-19 | 2019-08-13 | 深圳市一正科技有限公司 | 用于氟化反应的微通道反应器及其制备方法 |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3064058A (en) | 1961-04-07 | 1962-11-13 | Nepera Chemical Co Inc | Method of preparing fluorinated compounds |
GB2058067A (en) | 1979-09-08 | 1981-04-08 | Isc Chemicals Ltd | Process for the preparation of fluorinated aromatic compounds |
US4418229A (en) | 1981-04-15 | 1983-11-29 | Mallinckrodt, Inc. | Method for producing fluoronitrobenzene compounds |
JPS57197226A (en) | 1981-05-30 | 1982-12-03 | Dainippon Ink & Chem Inc | Preparation of aromatic fluorine compound |
CS246346B1 (cs) | 1985-07-23 | 1986-10-16 | Jiri Jilek | Způsob přípravy nového 4-fluor-2-nitrobenzonitrilu |
US5177275A (en) * | 1989-05-01 | 1993-01-05 | Pcr Group, Inc. | Reaction of substrate compounds with fluorine in an eductor |
JP2006001881A (ja) * | 2004-06-17 | 2006-01-05 | Fuji Photo Film Co Ltd | フッ素化有機化合物の製造法 |
DE102004044942A1 (de) | 2004-09-16 | 2006-03-30 | Esk Ceramics Gmbh & Co. Kg | Verfahren zum verformungsarmen Diffusionsschweißen von keramischen Komponenten |
CN102219638B (zh) * | 2010-04-16 | 2014-07-23 | 中国科学院上海有机化学研究所 | 一种烯基羧酸的氟化方法 |
CN102675015B (zh) * | 2012-06-11 | 2014-11-05 | 中国科学院上海有机化学研究所 | 羧酸脱羧氟代的方法 |
CN106397377B (zh) * | 2016-09-05 | 2019-04-05 | 中南大学 | 一种富电子五元杂环酸及其衍生物脱羧上氟的方法 |
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- 2020-03-24 EP EP20165425.8A patent/EP3786143A1/fr active Pending
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Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5420364A (en) * | 1992-07-09 | 1995-05-30 | Bayer Aktiengesellschaft | Process for the preparation of halogenated aromatic compounds |
WO2003064371A1 (fr) * | 2002-02-01 | 2003-08-07 | F2 Chemicals Limited | Synthese d'agents de fluoration |
WO2015050379A1 (fr) * | 2013-10-01 | 2015-04-09 | 광주과학기술원 | Nouveau dérivé de quinolinone et son utilisation |
CN108250176A (zh) * | 2016-12-19 | 2018-07-06 | 上海惠和化德生物科技有限公司 | 一种氟代碳酸乙烯酯的快速连续流合成工艺 |
CN110115966A (zh) * | 2019-06-19 | 2019-08-13 | 深圳市一正科技有限公司 | 用于氟化反应的微通道反应器及其制备方法 |
Non-Patent Citations (2)
Title |
---|
Aqueous fluorination of carboxylic acid salts;GRAKAUSKAS,V等;《Journal of Organic Chemistry》;19691231;2446-50 * |
GRAKAUSKAS,V等.Aqueous fluorination of carboxylic acid salts.《Journal of Organic Chemistry》.1969,2446-50. * |
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JP7216099B2 (ja) | 2023-01-31 |
US20210061737A1 (en) | 2021-03-04 |
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